The Structure of Acnistin B and the Immunosuppressive Effects of Acnistins A, B, and E

Luis, Javier G.; Echeverri, Fernándo; García, Féderico; Rojas, Marianela Chavarría

doi:10.1055/s-2006-959498

Cited by 23 publications

(20 citation statements)

References 5 publications

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“…On the other hand, the antistress activity of W. somnifera glycowithanolides (e.g. sitoindosides) has been linked to their antioxidant activity (231,232 (124). Coagulin H (7) isolated from W. coagulans also was a strong inhibitor of incorporation of […”

Section: Antistress Activitymentioning

confidence: 99%

Withanolides and Related Steroids

Misico

Nicotra

Oberti

et al. 2011

Progress in the Chemistry of Organic Natural Products Vol. 94

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Section: Antistress Activitymentioning

confidence: 99%

Withanolides and Related Steroids

Misico

Nicotra

Oberti

et al. 2011

Progress in the Chemistry of Organic Natural Products Vol. 94

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“…The withanolides are the most abundant and have been isolated from various genera of the family Solanaceae [3], [4], [5], [6], [7]. The withano-lides have been considered to be of great medicinal value since they display a wide spectrum of biological activity such as antimicrobial, antitumor, anti-inflammatory, hepatoprotective, immunomodulatory, cytotoxic, immunosuppressive and insect-antifeedant properties [7], [8], [9].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Epimeric Withaphysalins from Leaves ofAcnistus arborescens

Veras¹,

Bezerra²,

Braz-Filho³

et al. 2004

Planta med

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Phytochemical analysis of the leaves of Acnistus arborescens (Solanaceae) resulted in the isolation of two new epimeric withaphysalins (17S,20R,22R)-5beta,6beta: 18,20-diepoxy-4beta,18-dihydroxy-1-oxowitha-24-enolide (2, 18R and 18S), together with the known withaphysalin F (1, 18R and 18S). Their structures were established by spectroscopic methods, including 2D NMR data and comparison with literature data. Compounds 1 and 2 dis-played potent cytotoxic activities against several cancer cell lines with IC50 values in the range of 0.20 to 1.46 microg/mL for 1 and 0.89 to 8.08 microg/mL for 2. The strong cytotoxicity presented by 1 suggests that in this series of compounds, the 2,3-unsaturated ketone moiety is an important pharmacophoric unit. The cytotoxic activity seemed to be related to DNA synthesis inhibition, as revealed by the reduction of 5-bromo-2'-deoxyuridine incorporation after 24 hours of incubation on leukemic cells.

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“…The isolation and synthesis of withanolides have attracted great interest due to their diverse biological activities such as anti-inflammatory [11], antimicrobial [12], antitumoral [13] [14], antistress [15], antiulceral and hepatoprotective [16], antiparasitical [17], immunomodulatory [18], and insect-antifeedant properties [19]. Recently, it has been reported that these compounds exhibit inhibitory activities against cyclooxygenase-1 (COX-1) and -2 (COX-2) [20], acetylcholinesterase, and butyrylcholinesterase enzymes [21], and induction activity on quinone reductase [14] [22].…”

mentioning

confidence: 99%

Withanolides from Aureliana fasciculata var. fasciculata

Almeida-Lafetá

Ferreira

Emerenciano

et al. 2010

Helvetica Chimica Acta

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In the first phytochemical study of the Aureliana genus (Solanaceae), two new withanolides, 1 and 2, together with two known sterols, were isolated from the MeOH extract of the leaves of Aureliana fasciculata var. fasciculata. The structures were established as (4S,22R)-16a-acetoxy-5b,6b-epoxy-4b,17a-dihydroxy-1-oxowitha-2,24-dienolide (aurelianolide A) and (4S,22R)-16a-acetoxy-4b,17a-dihydroxy-1-oxowitha-2,5,24-trienolide (aurelianolide B). The new compounds possessed the unusual 16a,17a-dioxygenated group and were fully characterized by spectroscopic techniques, including 1 H-and Introduction. -The withasteroids comprise a group of naturally occurring C 28 -steroids characterized by an unaltered or a modified ergostane skeleton with a lactone or potential lactone ring in the C 9 side chain [1]. The most abundant type is designated usually as withanolide, and these compounds possess an a,b-unsaturated d-lactone ring in the side chain of the molecule. These steroid derivatives are frequently polyoxygenated, and biogenetic transformations can produce highly modified structures, both in the steroid nucleus and in the side chain, such as physalins, withaphysalins, acnistins, withanolides, ixocarpalactones, and perulactones [2]. To date, over 400 withasteroids have been reported which are restricted in distribution to the plant family Solanaceae occurring primarily in ca. 20 genera [1] [2]. However, the occurrence of steroidal lactones is not completely restricted to Solanaceae, whereas these compounds have also been found in soft coral from Minabea sp.

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The Structure of Acnistin B and the Immunosuppressive Effects of Acnistins A, B, and E

Abstract: The structure of the new withanolide:acnistin B, isolated from Dunalia solanacea, has been established by NMR experiments and the immunosuppressive effects of acnistins A, B and E on human lymphocytes have been measured.

Cited by 23 publications

References 5 publications

Withanolides and Related Steroids

Withanolides and Related Steroids

Cytotoxic Epimeric Withaphysalins from Leaves ofAcnistus arborescens

Withanolides from Aureliana fasciculata var. fasciculata

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